Once in a lifetime opportunity to acquire one of the last remaining unrestricted working farms in Northern Dutchess County, NY. Choice building sites, panoramic views and seclusion yet convenient to New York City, Metro North commuter train and nearby area amenities including Millerton, NY, Litchfield County, CT, Troutbeck Inn, Millbrook, NY and Silo Ridge.

Successful, turnkey inn located in the picturesque village of West Stockbridge, walking distance to shops, restaurants, and galleries. This unique property boasts nine spacious, well-appointed guest rooms, most with private outdoor entrances. Each room has a kitchenette and ensuite bathroom. Most rooms have gas fireplaces and private balconies, overlooking the manicured grounds. The Greylock suite is perfectly set up for long term stays, with a full kitchen, living room, and separate bedroom. For the innkeeper, there is a spacious owner's quarters, privately located on the top level of the inn, with its own separate entrance, full kitchen, laundry, and lots of charm.Close to all that the Berkshires have to offer, this is a great live/work opportunity in a highly desirable area.

Sited on the Housatonic River in Gt Barrington built in 2005/2014 the Barn exterior belies the contemporary interior w/ floor to ceiling windows overlooking the River; a seamless open floor plan on the main floor includes living/dining/ kitchen/fireplace/office/powder room/stairs to 422 sq.ft. loft & hallway to primary bedroom suite. Entire house has central ac. Two bedrooms on the ground floor share a stunning Alford marble bathroom. The entire lower level has radiant floor heat. One of the bedrooms serving as both office & sleeping accommodations w/ a sliding barn door opening to the one of a kind marble terrace overlooking the River. The ground floor is capped off by a laundry room, & all purpose gym/sauna/storage/extra sleeping. Two car garage w/ direct access to River Barn.

The Perfect Retreat! FOUR BROOKS FARM, owned by the De Kay Gilder Palmer Family since 1898, is now available. This exceptional property embodies idyllic country living in the heart of The Berkshires. This historic property consists of the Main House, Guest Wing, Barn with Tack Room, Roman Walled Garden with Sunrise/Sunset window, Stonewalls, Pastures, Trails & Views . Ready for restoration to former glory, many recent improvements have been completed. Rolling meadows, gardens, stone walls and views! Rich in history, with so much potential to be a cherished Berkshire retreat. Close proximity to notable area cultural attractions . Reportedly visited by notables such as Mark Twain and Grover Cleveland...

At the end of a long tree lined driveway, you'll find a fabulous 4 bedroom, 5 bath Dutch Gambrel with detached garage only minutes to Great Barrington. This spacious home is set on almost 5 sunny acres, which include a possible abutting building lot. This place has it all - great entertaining spaces, perfect cook's kitchen, fireplaces and private and peaceful outdoor gardens, along with a lovely screened-in porch to take in the gorgeous landscaping. Home built in 1989 with 2004 and 2019 renovations. A luscious hi-beamed master suite is on the first floor. Meticulously maintained so you can move right in!

Escape to tranquility in the Berkshires with this stunning 4000+ square foot residence boasting an open floor plan, 2 fireplaces, large sunroom, 2-car garage, formal dining and wrap-around front porch, offering both luxury and privacy. Featuring four bedrooms including a lavish primary suite with a fireplace, this home is designed for relaxation. Outside, a gunite pool and expansive stone patio create an idyllic retreat, complemented by a wall of glass overlooking the pool from the living space. Additional features include a finished basement and a third floor living room complete with a full bathroom and private office space, both providing additional space for recreation or relaxation. This is the perfect spot to embrace the epitome of New England living in this exquisite property.

Pristine, custom-built home in a lovely Lenox neighborhood. Close to downtown, this beautiful one-owner home on a corner lot has plenty of space to relax and enjoy the peaceful setting. Three beautifully appointed levels, with high-end finishes throughout, are thoughtfully laid out to include five bedrooms and four full baths. A true primary suite, with a luxurious soaking tub and expansive walk-in closet add to the comfort and convenience of the home, while the soaring ceilings and light-flooded rooms provide the wow factor. This home makes quite an impression the moment you walk in. A chef's kitchen overlooks a beautiful family room, with a gas fireplace and picture windows framing the view of the partially wooded lot. The dining room is also open to the kitchen, giving

Poised proudly on Main Street, Great Barrington, a few blocks from eateries, shops, and performance venues, this marvelous place affords an unparalleled residential and income opportunity. Purpose-built as an inn, its main house features nine bedrooms and a studio suite, while its carriage house contains two apartments. The sellers have rebuilt porches and staircases, added AC, installed insulation, refreshed cosmetics, remodeled the kitchen and public spaces, and added parking and gardens. Gracious spaces, high ceilings, light-welcoming windows, fireplaces, and architectural details create the ideal setting for a new owner's tastes and ideas. As a residence, this property in the heart of the Berkshires has the potential to support itself!

Poised proudly on the vibrant Main Street of Great Barrington, a few blocks from eateries, shops, and performance venues, the Wainwright Inn affords an unparalleled lifestyle and income opportunity. Purpose-built as an inn, its Victorian main house features nine guest rooms with baths en suite and an owners' suite, while its carriage house contains an apartment plus two guest rooms with baths en suite. The sellers have completed significant updates and improvements including AC, structural and cosmetic work, remodeling the kitchen, and adding parking and gardens (See Documents). Gracious spaces, high ceilings, light-welcoming windows, fireplaces, and historic architectural details create the ideal setting for a new owner's tastes and ideas. Strong financials, available upon request.

Poised proudly on the vibrant Main Street of Great Barrington, a few blocks from eateries, shops, and performance venues, the Wainwright Inn affords an unparalleled lifestyle and income opportunity. Purpose-built as an inn, its Victorian main house features nine guest rooms with baths en suite and an owners' suite, while its carriage house contains an apartment plus two guest rooms with baths en suite. The sellers have completed significant updates and improvements including AC, structural and cosmetic work, remodeling the kitchen, and adding parking and gardens (See Documents). Gracious spaces, high ceilings, light-welcoming windows, fireplaces, and historic architectural details create the ideal setting for a new owner's ideas. Financials available upon request. 2024 Taxes = $13,737.

WEST STOCKBRIDGE.....The location you've been waiting for!! Minutes from the Main Gate of Tanglewood, this mid century Contemporary has it all just waiting for you to put your personal touches on it. Main four bedroom residence with walls ofglass taking in the sweeping view, separate guest cottage, in-ground pool w/pool house all surrounded by 18+ private acres on both sides of the country lane!

Perched high on the hill and surrounded by more than 30 acres of land, this custom Timberpeg home overlooks breathtaking, wide-ranging vistas, and sunset views to the Catskills. The heart of the home is an open-floor plan kitchen and living area, flooded with natural light, creating a warm and inviting space. An impressive 31-foot stone fireplace, equipped with a wood stove insert adds a touch of rustic elegance and warmth.Three bedrooms, each featuring its own private ensuite bathroom ensures the utmost comfort and privacy for family or guests. Additionally, the convenience of an elevator provides effortless access to every floor.Conveniently located only 5 minutes to Chatham, 20 minutes to Hudson, and 30 minutes to Great Barrington. This extraordinary property not only offers a

Located on picturesque Mitchell St this property has a beautiful gentleness to it. It comprises of three separate contiguous lots (35.2 acres, 43.1 acres and 48.8 acres per assessor); access comes in off the southern most lot (43.10) and meanders through the property by a pond site, open meadows, old fruit trees and views of the hills around. The middle lot takes you in through a wooded area and opens up to a southwest view that just hits right. The north lot does have its own frontage but the main access does go into this lot as well and the views southeast are of catamount and hills around. Easily a three property development or a wonderful private compound. Come have a walk around.

FANTASTIC, UNUSUAL AND UNIQUE WATERFRONT OFFERING: THREE PROPERTIES ON OTIS RESERVOIR, the largest recreational lake in the state at 1085 acres. The three separately deeded properties included are: 183 Pine Road, a charming 4 bedroom cottage located 20 feet from the water's edge with a swimming area and three docks - lots of space for water toys; 185 Pine Road, a 2 bedroom contemporary cabin featuring a delightful covered deck overlooking the long lawn leading to the lake and the fourth dock; and finally 0 Pine Road, a vacant lot abutting both house lots with multiple potential uses - future guest house, garage and more. The combined properties offer 150 feet of beautiful lakefront and a total of 1.5 acres.

This stunning and immaculate home offers a blend of modern comforts and classic charm in a picturesque location with beautiful views. The blend of Contemporary design with Cape Cod style creates a timeless aesthetic that combines elegance with functionality. The tasteful renovation shows quality craftsmanship and attention to detail. The abundance of natural light from eastern and western exposure creates a warm and inviting ambiance while showcasing the scenic views. Top-of-the-line appliances in the gourmet kitchen for those who enjoy cooking and entertaining. The four bedrooms and 3.5 baths provide space for family or guests, offering comfort and privacy. The stunning four-season sunroom with walls of glass offers a serene space to relax and enjoy the beauty of each season. See Supp

Discover a lucrative investment opportunity with this contemporary 8000+ square foot dental building boasting two long-term leased suites and a strong cap rate. Equipped with an elevator and situated in a high-traffic commercial district, this property ensures stable rental income and convenient accessibility. With modern renovations and amenities, well laid out operatories, waiting rooms, reception stations, offices and ample parking, this building has it all. Secure this asset for a promising return on investment and future growth potential.

Maya Lin Masterpiece. Evoking the serenity and simplicity of the Japanese courtyard aesthetic, this extraordinary home, Maya Lin's first residential conception, stuns in the purity of its design and materials, in the singular curvilinear articulation of its roofline, and in the liberal use of fieldstone, slate, cherry, maple and ash in restrained architectural elements yielding a rich yet exquisitely understated ambience. The graceful rooflines reflect the swells and hollows of the distant hills, and define as well the interior spatial configuration and elevations. Upon entering through the front door a glimpse of the lovely central courtyard hosting Japanese maples and koi pond lies ahead. The main living area opens both to this intimate courtyard and to a deck with the inspiring view.

Just a very special property. Located between the Rockwell Museum and the Botanical Garden. You are moments from Tanglewood. Equidistant from Lenox and Great Barrington so it's easy to access the Berkshires wonderful restaurants. The main house has three bedrooms and two baths , while the guest cottage adds another bedroom, bath, and large living room. Gracious grounds are well landscaped. Adorable play house for little ones. Several various outbuildings. Garages for at least 5 cars.

Handsomely built with modern comfort and amenities. Meet Guests on the covered porch and welcome them into the first floor open kitchen and great room with stone fireplace. On the first floor is also the dining room, office, den, mudroom and breezy screened porch for summer drinks. First floor primary suite with sparkling ensuite bathroom and sitting room with fireplace is its own hideaway. Upstairs, three more large ensuite bedrooms for the crew. One-car garage located off the first floor for easy access to the kitchen, two oversized garages below. Located at the end of a shared private drive with similar homes, and maybe some new friends, this retreat will be home base for all of your Berkshire adventures.

INCREDIBLE OPPORTUNITY TO FINISH A 3-LEVEL, 6,000 SQUARE FOOT BERKSHIRE DREAM HOME ON 16 PRIVATE ACRES AND A TWO-BEDROOM GUEST HOUSE. ** DESIGN BY Woodhouse Timber Frame Company. ***CONSTRUCTION IN PROGRESS*** Completed: Surveys, land clearing, driveway installed, underground utilities, well, septic, house plans, building permits, privacy berm, foundation, framing, roughed-in plumbing, electric and propane heat, inground pool foundation, floor plans for 3 bedrooms, 4 baths, 2 kitchens, 2 family rooms, attached 2-car garage. GUEST HOUSE: Interior plans for 2 bedrooms, LR, kitchen, and bath over 2-bay garage.